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Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

✍ Scribed by Wolfgang Oppolzer; Eric Walther; Carlos Pérez Balado; Jef De Brabander

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 258 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02408-2

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✦ Synopsis

The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from Npropionylbornanesultam ent-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 ---) 7) followed by saponification of the sultam moiety (7 --) 4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61-71% overall yield.

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